#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/68/4506804.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4506804
loop_
_publ_author_name
'Vangala, Venu R.'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_publ_section_title
;
 Co-Crystals and Co-Crystal Hydrates of the Antibiotic Nitrofurantoin:
 Structural Studies and Physicochemical Properties
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5925
_journal_paper_doi               10.1021/cg300887p
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C13 H12 N5 O6'
_chemical_formula_weight         334.28
_chemical_name_common
;
 1:1/2:1 Cocrystal of nitrofurantoin, 4,4'-bipyridyl and water
;
_chemical_name_systematic
;
 1:0.5:1 Cocrystal of nitrofurantoin, 4,4'-bipyridyl and water
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.86(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.804(6)
_cell_length_b                   6.7822(14)
_cell_length_c                   13.672(3)
_cell_measurement_reflns_used    3430
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      31.0778
_cell_measurement_theta_min      2.1561
_cell_volume                     2905.5(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16577
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, Rigaku 2007)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.241
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+4.9189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1544
_reflns_number_gt                2510
_reflns_number_total             2556
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300887p_si_001.cif
_cod_data_source_block           nf-4,4'-bipyridyl-monohydrate(1:0.5:1)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2905.5(10)
_cod_original_sg_symbol_H-M      'C 2 /c'
_cod_database_code               4506804
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.11829(5) 0.6031(3) 0.41073(12) 0.0299(4) Uani 1 1 d .
N2 N 0.20424(7) 0.5344(3) 0.42667(15) 0.0291(5) Uani 1 1 d .
O4 O 0.26085(6) 0.5125(3) 0.60478(13) 0.0340(5) Uani 1 1 d .
N3 N 0.24655(7) 0.4938(3) 0.43289(15) 0.0298(5) Uani 1 1 d .
O5 O 0.34411(6) 0.3419(3) 0.37609(15) 0.0416(5) Uani 1 1 d .
C4 C 0.07574(8) 0.6190(4) 0.37633(19) 0.0284(6) Uani 1 1 d .
O3 O 0.01079(6) 0.6720(3) 0.41812(14) 0.0396(5) Uani 1 1 d .
N4 N 0.31177(7) 0.4248(3) 0.50934(16) 0.0310(5) Uani 1 1 d .
N1 N 0.04972(7) 0.6549(3) 0.44823(16) 0.0332(5) Uani 1 1 d .
N5 N 0.39112(7) 0.3965(3) 0.63450(17) 0.0336(5) Uani 1 1 d .
C10 C 0.46529(8) 0.3559(4) 0.62400(19) 0.0309(6) Uani 1 1 d .
H10A H 0.4862 0.3269 0.5842 0.037 Uiso 1 1 calc R
C6 C 0.27191(8) 0.4817(4) 0.52549(19) 0.0285(6) Uani 1 1 d .
C12 C 0.44464(8) 0.4345(4) 0.7788(2) 0.0306(6) Uani 1 1 d .
H12A H 0.4513 0.4635 0.8477 0.037 Uiso 1 1 calc R
C11 C 0.47731(8) 0.3955(4) 0.72577(19) 0.0283(6) Uani 1 1 d .
O2 O 0.06675(6) 0.6695(3) 0.53611(14) 0.0445(5) Uani 1 1 d .
C1 C 0.13600(8) 0.5679(4) 0.32736(18) 0.0293(6) Uani 1 1 d .
C5 C 0.18132(8) 0.5347(4) 0.33940(19) 0.0300(6) Uani 1 1 d .
H5B H 0.1943 0.5130 0.2828 0.036 Uiso 1 1 calc R
C13 C 0.40252(9) 0.4313(4) 0.7320(2) 0.0320(6) Uani 1 1 d .
H13A H 0.3808 0.4546 0.7704 0.038 Uiso 1 1 calc R
C7 C 0.31306(9) 0.3949(4) 0.4101(2) 0.0328(6) Uani 1 1 d .
C8 C 0.26912(8) 0.4381(4) 0.35285(19) 0.0315(6) Uani 1 1 d .
H8A H 0.2697 0.5475 0.3052 0.038 Uiso 1 1 calc R
H8B H 0.2563 0.3201 0.3169 0.038 Uiso 1 1 calc R
C9 C 0.42246(8) 0.3598(4) 0.5826(2) 0.0327(6) Uani 1 1 d .
H9A H 0.4148 0.3350 0.5134 0.039 Uiso 1 1 calc R
C2 C 0.10521(8) 0.5640(4) 0.24472(19) 0.0312(6) Uani 1 1 d .
H2B H 0.1095 0.5434 0.1784 0.037 Uiso 1 1 calc R
C3 C 0.06578(8) 0.5963(4) 0.27634(19) 0.0305(6) Uani 1 1 d .
H3A H 0.0383 0.6011 0.2364 0.037 Uiso 1 1 calc R
O6 O 0.17624(8) 0.3290(3) 0.12285(15) 0.0434(5) Uani 1 1 d .
H4 H 0.3380(10) 0.408(5) 0.559(2) 0.045(8) Uiso 1 1 d .
H6B H 0.1977(19) 0.376(8) 0.095(4) 0.13(2) Uiso 1 1 d .
H6A H 0.148(2) 0.339(9) 0.070(4) 0.15(2) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C4 O1 C1 104.57(19) .
C5 N2 N3 117.1(2) .
N2 N3 C6 119.0(2) .
N2 N3 C8 127.9(2) .
C6 N3 C8 112.8(2) .
C3 C4 O1 112.7(2) .
C3 C4 N1 131.1(2) .
O1 C4 N1 116.2(2) .
C6 N4 C7 112.4(2) .
O2 N1 O3 124.2(2) .
O2 N1 C4 118.7(2) .
O3 N1 C4 117.1(2) .
C13 N5 C9 117.4(2) .
C9 C10 C11 119.0(2) .
O4 C6 N4 127.3(2) .
O4 C6 N3 126.5(2) .
N4 C6 N3 106.2(2) .
C13 C12 C11 120.4(2) .
C12 C11 C10 116.9(2) .
C12 C11 C11 121.6(3) 2_656
C10 C11 C11 121.5(3) 2_656
C2 C1 O1 110.6(2) .
C2 C1 C5 130.9(2) .
O1 C1 C5 118.4(2) .
N2 C5 C1 120.2(2) .
N5 C13 C12 122.6(3) .
O5 C7 N4 125.6(3) .
O5 C7 C8 126.8(2) .
N4 C7 C8 107.5(2) .
N3 C8 C7 101.1(2) .
N5 C9 C10 123.7(2) .
C1 C2 C3 107.0(2) .
C4 C3 C2 105.0(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.359(3) .
O1 C1 1.376(3) .
N2 C5 1.287(3) .
N2 N3 1.362(3) .
O4 C6 1.214(3) .
N3 C6 1.382(3) .
N3 C8 1.458(3) .
O5 C7 1.216(3) .
C4 C3 1.358(4) .
C4 N1 1.410(3) .
O3 N1 1.241(3) .
N4 C6 1.379(3) .
N4 C7 1.379(3) .
N1 O2 1.234(3) .
N5 C13 1.341(4) .
N5 C9 1.342(4) .
C10 C9 1.383(4) .
C10 C11 1.404(4) .
C12 C13 1.382(4) .
C12 C11 1.391(4) .
C11 C11 1.481(5) 2_656
C1 C2 1.363(4) .
C1 C5 1.440(4) .
C7 C8 1.509(4) .
C2 C3 1.412(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146220
